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Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine


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Title: Stereoselective synthesis of 3-deoxy-piperidine iminosugars from l-lysine
Authors: Moriyama, Noriaki / Matsumura, Yoshihiro / Kuriyama, Masami / Onomura, Osamu
Issue Date: 11-Dec-2009
Publisher: Elsevier Ltd.
Citation: Tetrahedron: Asymmetry, 20(23), pp.2677-2687; 2009
Abstract: A new method using electrochemical oxidation and/or OsO4 oxidation has been used for the stereoselective synthesis of 2,3,6-trihydroxylated (5S)-piperidine derivatives. The electrochemical method was successively used for the conversion of N-protected piperidines to N-protected 1-methoxypiperidines and for the conversion of 2,3-didehydro-1-methoxypiperidine derivatives to 2,3-trans-1,2,3-triacetoxypiperidine derivatives. These triacetates were easily transformed into (2S,3S)-6-triacetoxy-(5S)-methylpiperidine and (2R,3R)-6-triacetoxy-(5S)-methylpiperidine. In addition, the 2,3-cis-dihydroxylation of 2,3-didehydro-1-methoxypiperidine derivatives with OsO4 afforded (2R,3S)-6-triacetoxy-(5S)-methylpiperidine and (2S,3R)-6-triacetoxy-(5S)-methylpiperidine.
URI: http://hdl.handle.net/10069/23032
ISSN: 09574166
DOI: 10.1016/j.tetasy.2009.11.028
Rights: Copyright © 2009 Elsevier Ltd All rights reserved.
Type: Journal Article
Text Version: author
Appears in Collections:Articles in academic journal

Citable URI : http://hdl.handle.net/10069/23032

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